This weekend, I plan to do Kaaterskill High Peak.  This is another of the "trailless" peaks, but in reality, the majority of it is either the Long Path or snowmobile trails.  Looking at the elevation for this, there's really not much steep until the very end.  I may try to cut a little bit of distance off of the mapped 7.6 miles by bushwhacking when I get to the plateau.

Assuming that I still have something in the tank after this peak, I'll go and do Windham High Peak.  This one is trailed, and again, not that steep except for one point on the way up.  The way I'm planning on going up, it's only 6 miles too, so that would bring my mileage for the day to 13ish.  If I can't find parking where I want, I know there'll be parking at the end of the escarpment trail, and that only adds about .8 miles.  It's been a while since I've done that much mileage, but considering most of the trails are going to be moderate slope (most at 10% or lower slope) it should be doable.